Tag: M.W=150-200

Kalugin, V. E. published the artcileSynthesis of 5-aminopyrido[3′,2′:4,5]thieno[3,2-c]isoquinoline derivatives from 3-cyanopyridine-2(1H)-thiones and 2-(chloromethyl)benzamide, Formula: C8H6ClN, the publication is Russian Chemical Bulletin (2018), 67(8), 1492-1499, database is CAplus.

Substituted 5-aminopyrido[3′,2′:4,5]thieno[3,2-c]isoquinolines were synthesized by condensation of substituted 3-cyanopyridine-2(1H)-thiones with 2-(chloromethyl)benzamide and subsequent treatment of the condensation products with potassium tert-butoxide. Oxidation of the condensation products to sulfoxides and sulfones followed by treatment of these compounds with potassium tert-butoxide gave substituted 5-aminopyrido[3′,2′:4,5]thieno[3,2-c]isoquinoline 11-oxides and substituted 5-aminopyrido[3′,2′:4,5]thieno[3,2-c]isoquinoline 11,11-dioxides in good yields.

Russian Chemical Bulletin published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Formula: C8H6ClN.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Kalugin, V. E. published the artcileThe synthesis of 3-cyano-2-(organylamino)thieno[3,2-c]isoquinoline derivatives, Quality Control of 612-13-5, the publication is Russian Chemical Bulletin (2019), 68(3), 588-596, database is CAplus.

A method for the preparation of 3-cyano-2-(organylamino)thieno[3,2-c]isoquinoline derivatives was developed. Alkylation of (2,2-dicyano-1-organylaminovinyl)thiolates with Me 2-(chloromethyl)benzoate or N-substituted 2-(chloromethyl)benzamides with the subsequent treatment of the alkylation products with potassium tert-butoxide gave 3-cyano-2-(organylamino)thieno[3,2-c]isoquinolin-5(4H)-ones. In the case of utilization of (chloromethyl)benzonitrile in this synthesis, 5-amino-3-cyano-2-organylaminothieno[3,2-c]iso-quinolines were obtained.

Russian Chemical Bulletin published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Quality Control of 612-13-5.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Kalugin, V. E. published the artcileThe synthesis of substituted 5-aminopyrido[3′,2′:4,5]thieno[3,2-c]isoquinolines and their sulfinyl and sulfonyl derivatives, Formula: C8H6ClN, the publication is Russian Chemical Bulletin (2018), 67(5), 902-911, database is CAplus.

5-Aminopyrido[3′,2′:4,5]thieno[3,2-c]isoquinolines were synthesized via alkylation of 3-cyanopyridine-2(1H)-thiones with 2-(chloromethyl)benzonitrile followed by treatment of the products with potassium tert-butoxide. The oxidation of the alkylated products to corresponding sulfoxides or sulfones followed by treatment with potassium tert-butoxide provided the corresponding 11-oxides or 11,11-dioxides.

Russian Chemical Bulletin published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Formula: C8H6ClN.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Kalugin, Victor E. published the artcileA convenient synthesis of benzofuro[3,2-c]isoquinolines and naphtho[1′,2′:4,5]furo[3,2-c]isoquinolines, Product Details of C8H6ClN, the publication is Tetrahedron Letters (2011), 52(14), 1557-1560, database is CAplus.

A convenient method for the preparation of benzofuro[3,2-c]isoquinoline derivatives is described. The condensation reaction of Me 2-(chloromethyl)benzoate with substituted salicylonitriles (I) and intramol. cyclization of the resulting substituted Me 2-[(2-cyanobenzyl)oxy]benzoates using potassium tert-butoxide results in substituted benzofuro[3,2-c]isoquinolin-5(6H)-ones. The same sequence of reactions starting from 2-(chloromethyl)benzonitrile and I gave substituted 5-aminobenzofuro[3,2-c]isoquinolines. In addition, this method is useful for the synthesis of other heterocycles. For example, using 1-cyano-2-naphthol, instead of I, gives naphtho[1′,2′:4,5]furo[3,2-c]isoquinolines.

Tetrahedron Letters published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Product Details of C8H6ClN.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Xue, Ya-Ping published the artcileDesign of Nitrilases with Superior Activity and Enantioselectivity towards Sterically Hindered Nitrile by Protein Engineering, Product Details of C8H6ClNO, the publication is Advanced Synthesis & Catalysis (2015), 357(8), 1741-1750, database is CAplus.

The enantioselective hydrolysis of ortho-chloromandelonitrile with nitrilase is one of the most attractive approaches to prepare (R)-ortho-chloromandelic acid. To date, efforts to develop this nitrilase-mediated process were plagued by either insufficient ee_p (enantiomeric excess of product) or low activity due to the steric hindrance from the ortho-substituted substrate. To improve the nitrilase potential for producing (R)-ortho-chloromandelic acid, an enhancement of both activity and enantioselectivity towards sterically hindered nitriles would be highly desirable. Mol. docking of the (R)-ortho-chloromandelonitrile into the active site of wild-type 2A6 nitrilase (nitA) allowed the identification of proximal nitA active site residues. Several residues (52, 132, 189 and 190) were selected as targets for single and double point mutation to improve nitA activity and enantioselectivity towards ortho-chloromandelonitrile. Targeted mutagenesis yielded several nitA variants with superior activity and enantioselectivity. The best mutant T132A/F189T exhibited a 4.37-fold higher specific activity (7.39 U/mg) towards ortho-chloromandelonitrile than the wild-type nitA. More importantly, the enantioselectivity (E) was improved from 17.34 to >200, resulting in a highly enantiopure product. Mol. docking experiments further support the enhanced activity and enantioselectivity shown exptl. and the structural effects of this amino acid substitution on the active site of nitA are provided. The amino acids at sites 189 and 132 determine the activity and enantioselectivity towards ortho-chloromandelonitrile. With mutant T132A/F189T as a catalyst, a maximum of 450 mM of (R)-ortho-chloromandelic acid was produced with a 90% conversion and >99% ee_p within 3 h. This is the first time that a high productivity of (R)-ortho-chloromandelic acid of up to 671.76 g L^-1 d^-1 using a nitrilase-mediated approach is reported. The engineered T132A/F189T variant represents a promising and competitive biocatalyst for practical application in synthesizing (R)-ortho-chloromandelic acid.

Advanced Synthesis & Catalysis published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C11H15NO2, Product Details of C8H6ClNO.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Yin, Shu-Qiang published the artcilePreparation of S14161 and its analogues and the discovery of 6-bromo-8-ethoxy-3-nitro-2H-chromene as a more potent antitumor agent in vitro, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Bioorganic & Medicinal Chemistry Letters (2013), 23(11), 3314-3319, database is CAplus and MEDLINE.

The small chem. compound 8-ethoxy-2-(4-fluorophenyl)-3-nitro-2H-chromene (S14161) was recently identified as an inhibitor of the phosphoinositide 3-kinase (PI3K). In the present study, the authors designed a novel synthesis of S14161 and prepared a series of its analogs via the oxa-Michael-Henry reaction in the presence of catalytic amounts of l-proline and triethylamine. Further structural simplification led to the identification of 6-bromo-8-ethoxy-3-nitro-2H-chromene (I, BENC-511) that exhibited potent antiproliferative activities against a panel of 12 tumor cell lines. Compared with S14161, BENC-511 was more potent in blocking the AKT phosphorylation and inducing cancer cell apoptosis. BENC-511 also displayed more potent effects on human umbilical vein epithelial cells (HUVEC) migration, suggesting its anti-angiogenesis activity.

Bioorganic & Medicinal Chemistry Letters published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C10H10O2, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Kumar, Saurabh published the artcileAIBN-Initiated Denitrative Cross-Coupling Reactions of β-Nitrostyrenes with Sulfonyl Hydrazides/Disulfides: A Metal-free Approach towards Vinyl Sulfones, Computed Properties of 5153-73-1, the publication is Asian Journal of Organic Chemistry (2018), 7(2), 359-362, database is CAplus.

A practical and metal free approach involving denitrative coupling of β-nitrostyrenes and sulfonyl hydrazides/disulfides by AIBN (azobisisobutyronitrile) was developed to accomplish the synthesis of vinyl sulfones I [R = Ph, 4-ClC₆H₄, 2-thienyl, etc.; R¹ = 4-MeC₆H₄, Bn, 2-naphthyl, etc.]. The method employed easily accessible starting materials and was endowed with a broad substrate scope, functional group tolerance and high yields.

Asian Journal of Organic Chemistry published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Computed Properties of 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Ambala, Srinivas published the artcileMetal-free, room temperature, acid-K₂S₂O₈ mediated method for the nitration of olefins: an easy approach for the synthesis of nitroolefins, Quality Control of 5153-73-1, the publication is RSC Advances (2019), 9(52), 30428-30431, database is CAplus and MEDLINE.

A simple, room temperature method for the nitration of olefins by using inexpensive sodium nitrite as a source of nitro groups in the presence of trifluoroacetic acid (TFA) and potassium persulfate (K₂S₂O₈) under an open atm. Styrenes and mono-substituted olefins give stereo-selective corresponding E-nitroolefins under optimized conditions, however, 1,1-bisubstituted olefins give a mixture of E- and Z-nitroolefins. The optimized conditions work well with electron-donating, electron-withdrawing, un-substituted and heterocyclic styrenes and mono-substituted olefins and gave corresponding nitroolefins with good to excellent yields.

RSC Advances published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Quality Control of 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Janssen-Mueller, Daniel published the artcileAnnulation of o-Quinodimethanes through N-Heterocyclic Carbene Catalysis for the Synthesis of 1-Isochromanones, Safety of 2-(Chloromethyl)benzonitrile, the publication is Organic Letters (2016), 18(17), 4444-4447, database is CAplus and MEDLINE.

The activation of 2-(bromomethyl)benzaldehydes using N-heterocyclic carbenes represents a novel approach to the generation of o-quinodimethane (o-QDM) intermediates. Coupling with ketones such as phenylglyoxylates, isatins, or trifluoromethyl ketones via [4 + 2] annulation gives access to functionalized 1-isochromanones.

Organic Letters published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Safety of 2-(Chloromethyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Castro, E. A. published the artcileStructure and reactivity of arylcyanohydrins, Related Products of nitriles-buliding-blocks, the publication is Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, Biochemie, Biophysik, Biologie (1974), 29(3-4), 209-12, database is CAplus.

The relation between structure and reactivity was examined for 18 RCH(OH)CN (I, R = substituted phenyl) by CNDO/2 calculation of the stability of I (dissociation constant for I �RCHO + HCN) and of at. energy terms.

Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, Biochemie, Biophysik, Biologie published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Related Products of nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts